Reactions of 3-Chloro-2H-thiete 1,1-Dioxide

Article abstract of DOI:10.1021/jo00187a021

3-Chloro-2H-thiete 1,1-dioxide, prepared by dichlorination of thietane 1,1-dioxide followed by dehydrochlorination, reacts with carbanions, amines, alcohols, and thiols to give 3-substituted thietane or 2H-thiete 1,1-dioxides.For example, reaction with the anion of dimethyl or diethyl malonate gives 3-thietane 1,1-dioxide. 3-Chloro-2H-thiete 1,1-dioxide also undergoes Diels-Ader reactions with butadiene and 1,3-diphenylisobenzofuran. 2,3-Dibromothietane 1,1-dioxide, 2,3-dibromo-3-chlorothietane 1,1-dioxide, 2-bromo-2H-thiete 1,1-dioxide, and 2-bromo-3-chloro-2H-thiete 1,1-dioxide also have been prepared.